pyrazine-2-carboxamide

• ChemBase编号: 223
• 分子式: C5H5N3O
• 平均质量: 123.1127
• 单一同位素质量: 123.0432618
• SMILES: O=C(N)c1nccnc1
• Canonical SMILES: NC(=O)c1cnccn1
• InChI: InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
• InChIKey: IPEHBUMCGVEMRF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: pyrazine-2-carboxamide
• IUPAC传统名: pyrazinamide
• 商标名: Aldinamid; Aldinamide; Braccopiral; Corsazinmid; Dipimide; Eprazin; Farmizina; Isopas; Lynamide; Novamid; Pezetamid; Piraldina; Pirilene; Prazina; Pyrafat; Pyramide; Pyrazide; Pyrazinamide BP 2000; Rifater; Rozide; Tebrazid; Tebrazio; Unipyranamide; Zinamide; Zinastat; pms-Pyrazinamide
• 别名: Pirazinecarboxamide; D-50; Piraldina; Tebrazid; Zinamide; Pyrazinamide; Pyrazinecarboxamide; pyrazine-2-carboxamide; Pezetamid; Pyrafat; 2-Carbamoylpyrazine; Pyrazine-2-carboxamide 99%; Pyrazinecarboxylic acid amide; Pyrazinecarboxamide; Pyrazinoic acid amide; PZA; Pyrazineamide; Pyrazine carboxylamide; Pyrazinamdie; Pirazinamid; Pirazimida; Pyrazinamide

登记号

• CAS号: 98-96-4
• EC号: 202-717-6
• MDL号: MFCD00006132
• Beilstein号: 112306
• PubChem SID: 24887930; 24278648; 46507478; 160963686
• PubChem CID: 1046
• CHEBI ID: 45285
• ATC码: J04AK01
• CHEMBL: 614
• Chemspider ID: 1017
• DrugBank ID: DB00339
• KEGG ID: D00144
• 美国药典/FDA物质标识码: 2KNI5N06TI
• 维基百科标题: Pyrazinamide
• Medline Plus: a682402

理论计算性质

JChem

• Acid pKa: 13.059009
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -1.2256087
• LogD (pH = 7.4): -1.2256075
• Log P: -1.2256085
• 摩尔折射率: 30.4506 cm^3
• 极化性: 11.437884 Å^3
• 极化表面积: 68.87 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.71
• LOG S: -0.12
• 溶解度: 9.37e+01 g/l

分子性质

理化性质

• 溶解度: 1.5E+004 mg/L; DMSO
• 外观: White Solid
• 熔点: 189°C; 189-191 °C; 189-191 °C(lit.); 189-191°C; 189-191°C
• 疏水性(logP): -1

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: Irritant
• RTECS编号: UQ2275000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 给药途径: Oral
• 生物利用度: >90%
• 排泄: Renal
• 半衰期: 9 to 10 hours
• 代谢: Hepatic
• 妊娠期药物分类: C

产品相关信息

• 纯度: ≥99.0% (N); 95+%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C5H5N3O

详细说明

MP Biomedicals - 05217986

MP Biomedicals Rare Chemical collection

DrugBank - DB00339

• Drug Groups: approved
• Description: A pyrazine that is used therapeutically as an antitubercular agent.
• Indication: For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents.
• Pharmacology: Pyrazinamide kills or stops the growth of certain bacteria that cause tuberculosis (TB). It is used with other drugs to treat tuberculosis. It is a highly specific agent and is active only against Mycobacterium tuberculosis. In vitro and in vivo, the drug is active only at a slightly acid pH. Pyrazinamie gets activated to Pyrazinoic acid in the bacilli where it interferes with fatty acid synthase FAS I. This interferes with the bacteriums ability to synthesize new fatty acids, required for growth and replication.
• Toxicity: Side effects include liver injury, arthralgias, anorexia, nausea and vomiting, dysuria,malaise and fever, sideroblastic anemia, adverse effects on the blood clotting mechanism or vascular integrity, and hypersensitivity reactions such as urticaria, pruritis and skin rashes.
• Affected Organisms: Mycobacterium tuberculosis
• Biotransformation: Hepatic.
• Absorption: Rapidly and well absorbed from the gastrointestinal tract.
• Half Life: 9-10 hours (normal conditions)
• Protein Binding: ~10% (bound to plasma proteins)
• Elimination: Approximately 70% of an oral dose is excreted in the urine, mainly by glomerular filtration within 24 hours
• References: Controlled trial of four thrice-weekly regimens and a daily regimen all given for 6 months for pulmonary tuberculosis. Lancet. 1981 Jan 24;1(8213):171-4. [Pubmed] ; Controlled clinical trial of 4 short-couse regimens of chemotherapy (three 6-month and one 8-month) for pulmonary tuberculosis. Tubercle. 1983 Sep;64(3):153-66. [Pubmed] ; A controlled trial of 6 months' chemotherapy in pulmonary tuberculosis. Final report: results during the 36 months after the end of chemotherapy and beyond. British Thoracic Society. Br J Dis Chest. 1984 Oct;78(4):330-6. [Pubmed] ; Yee D, Valiquette C, Pelletier M, Parisien I, Rocher I, Menzies D: Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am J Respir Crit Care Med. 2003 Jun 1;167(11):1472-7. Epub 2003 Jan 31. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1762

Research Area: Infection
Biological Activity:
Pyrazinamide (Pyrazinoic acid amide) is an agent used to treat tuberculosis. M. tuberculosis has the enzyme pyrazinamidase which is only active in acidic conditions. Pyrazinamidase converts pyrazinamide (Pyrazinoic acid amide) to the active form, pyrazinoic acid which accumulates in the bacilli. Pyrazinoic acid inhibits the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids although this has been discounted. [1]

Sigma Aldrich - P7136

包装
10, 25, 100 g in poly bottle
Application
Pyrazinamide is used therapeutically as an antitubercular agent. Pyrazinamide is used to form polymeric copper complexes, create pyrazine carboxamide scaffolds useful as FXs inhibitors, and as a component of mycobacteria identification kits. It is used to study liver toxicity prevention 1 and mechanisms of resistance 2.
Pyrazinamide is used to form polymeric copper complexes, create pyrazine carboxamide scaffolds useful as FXs inhibitors, and as a component of mycobacteria identification kits.
Biochem/physiol Actions
The active moiety of pyrazinamide is pyrazinoic acid (POA). POA is thought to disrupt membrane energetics and inhibit membrane transport function at acid pH in Mycobacterium tuberculosis. Iron enhances the antituberculous activity of pyrazinamide 3. Pyrazinamide and its analogs have been shown to inhibit the activity of purified FAS I.

Toronto Research Chemicals - P840600

Antibacterial (tuberculostatic).

参考文献

• Controlled trial of four thrice-weekly regimens and a daily regimen all given for 6 months for pulmonary tuberculosis. Lancet. 1981 Jan 24;1(8213):171-4. Pubmed
• Controlled clinical trial of 4 short-couse regimens of chemotherapy (three 6-month and one 8-month) for pulmonary tuberculosis. Tubercle. 1983 Sep;64(3):153-66. Pubmed
• A controlled trial of 6 months' chemotherapy in pulmonary tuberculosis. Final report: results during the 36 months after the end of chemotherapy and beyond. British Thoracic Society. Br J Dis Chest. 1984 Oct;78(4):330-6. Pubmed
• Yee D, Valiquette C, Pelletier M, Parisien I, Rocher I, Menzies D: Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am J Respir Crit Care Med. 2003 Jun 1;167(11):1472-7. Epub 2003 Jan 31. Pubmed
• http://en.wikipedia.org/wiki/Pyrazinamide
• Weiner, I.M., et al.: J. Pharmacol. Exp. Ther., 180, 411 (1972)
• Feldner, E., et al.: Anal. Profiles Drug Subs., 12, 433 (1983)